CA1061800A - Process for preparing iminodiacetonitrile - Google Patents
Process for preparing iminodiacetonitrileInfo
- Publication number
- CA1061800A CA1061800A CA248,577A CA248577A CA1061800A CA 1061800 A CA1061800 A CA 1061800A CA 248577 A CA248577 A CA 248577A CA 1061800 A CA1061800 A CA 1061800A
- Authority
- CA
- Canada
- Prior art keywords
- aqueous
- hcn
- reaction zone
- formaldehyde
- continuous reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- BSRDNMMLQYNQQD-UHFFFAOYSA-N iminodiacetonitrile Chemical compound N#CCNCC#N BSRDNMMLQYNQQD-UHFFFAOYSA-N 0.000 title claims abstract description 63
- 238000004519 manufacturing process Methods 0.000 title abstract description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 146
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims abstract description 78
- 238000006243 chemical reaction Methods 0.000 claims abstract description 69
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims abstract description 61
- 238000000034 method Methods 0.000 claims abstract description 32
- 239000002253 acid Substances 0.000 claims abstract description 27
- 239000011541 reaction mixture Substances 0.000 claims abstract description 23
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims abstract description 17
- 230000008569 process Effects 0.000 claims abstract description 16
- 239000004312 hexamethylene tetramine Substances 0.000 claims abstract description 15
- 239000008098 formaldehyde solution Substances 0.000 claims abstract description 12
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims abstract description 11
- 235000019256 formaldehyde Nutrition 0.000 claims description 43
- 229960004279 formaldehyde Drugs 0.000 claims description 42
- 229960004011 methenamine Drugs 0.000 claims description 12
- 238000010924 continuous production Methods 0.000 claims description 6
- 239000003381 stabilizer Substances 0.000 claims 2
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 abstract description 24
- 239000000243 solution Substances 0.000 abstract description 24
- 239000007864 aqueous solution Substances 0.000 abstract description 18
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 4
- -1 alkali metal salt Chemical class 0.000 abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 4
- 230000000087 stabilizing effect Effects 0.000 abstract description 2
- 238000002156 mixing Methods 0.000 description 33
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 28
- 239000000203 mixture Substances 0.000 description 25
- 238000003860 storage Methods 0.000 description 18
- 239000000047 product Substances 0.000 description 14
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000376 reactant Substances 0.000 description 8
- DFNYGALUNNFWKJ-UHFFFAOYSA-N aminoacetonitrile Chemical compound NCC#N DFNYGALUNNFWKJ-UHFFFAOYSA-N 0.000 description 7
- 229910021529 ammonia Inorganic materials 0.000 description 7
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 7
- 239000004471 Glycine Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 5
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 5
- 235000011130 ammonium sulphate Nutrition 0.000 description 5
- 235000011149 sulphuric acid Nutrition 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000002844 continuous effect Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229910000881 Cu alloy Inorganic materials 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- LJAIDEYQVIJERM-UHFFFAOYSA-N 2-[bis(cyanomethyl)amino]acetonitrile Chemical compound N#CCN(CC#N)CC#N LJAIDEYQVIJERM-UHFFFAOYSA-N 0.000 description 1
- GOLXRNDWAUTYKT-UHFFFAOYSA-N 3-(1H-indol-3-yl)propanoic acid Chemical compound C1=CC=C2C(CCC(=O)O)=CNC2=C1 GOLXRNDWAUTYKT-UHFFFAOYSA-N 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229940010556 ammonium phosphate Drugs 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- HAXVIVNBOQIMTE-UHFFFAOYSA-L disodium;2-(carboxylatomethylamino)acetate Chemical compound [Na+].[Na+].[O-]C(=O)CNCC([O-])=O HAXVIVNBOQIMTE-UHFFFAOYSA-L 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- WUWHFEHKUQVYLF-UHFFFAOYSA-M sodium;2-aminoacetate Chemical compound [Na+].NCC([O-])=O WUWHFEHKUQVYLF-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/611,369 US3988360A (en) | 1973-11-15 | 1975-09-08 | Process for preparing iminodiacetonitrile |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1061800A true CA1061800A (en) | 1979-09-04 |
Family
ID=24448748
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA248,577A Expired CA1061800A (en) | 1975-09-08 | 1976-03-23 | Process for preparing iminodiacetonitrile |
Country Status (10)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2942437A1 (de) | 1979-10-20 | 1981-04-23 | Degussa Ag, 6000 Frankfurt | Verfahren zur herstellung von iminodiacetonitril |
| EP2132164A1 (de) * | 2007-03-01 | 2009-12-16 | Basf Se | Verfahren zur herstellung von aminonitrilen |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1275593A (fr) * | 1960-12-02 | 1961-11-10 | Degussa | Procédé pour produire le nitrile imino-diacétique |
| US3167580A (en) * | 1962-04-12 | 1965-01-26 | American Cyanamid Co | Process for the preparation of iminodiacetonitrile |
| US3412137A (en) * | 1965-10-14 | 1968-11-19 | Geigy Chemical Company | Process for the preparation of nitriles |
| US3886198A (en) * | 1973-12-13 | 1975-05-27 | Grace W R & Co | Process for preparing iminodiacetonitrile |
-
1976
- 1976-03-23 CA CA248,577A patent/CA1061800A/en not_active Expired
- 1976-08-19 IE IE1846/76A patent/IE43417B1/en unknown
- 1976-09-01 NL NL7609714A patent/NL7609714A/xx not_active Application Discontinuation
- 1976-09-03 BE BE170368A patent/BE845867A/xx not_active IP Right Cessation
- 1976-09-04 DE DE2639874A patent/DE2639874C2/de not_active Expired
- 1976-09-06 SE SE7609835A patent/SE441266B/xx unknown
- 1976-09-06 IT IT26915/76A patent/IT1065479B/it active
- 1976-09-07 FR FR7626920A patent/FR2322858A1/fr active Granted
- 1976-09-07 JP JP51106336A patent/JPS6010023B2/ja not_active Expired
- 1976-09-08 GB GB37231/76A patent/GB1561144A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SE441266B (sv) | 1985-09-23 |
| IE43417B1 (en) | 1981-02-25 |
| FR2322858A1 (fr) | 1977-04-01 |
| GB1561144A (en) | 1980-02-13 |
| DE2639874A1 (de) | 1977-03-17 |
| SE7609835L (sv) | 1977-03-09 |
| NL7609714A (nl) | 1977-03-10 |
| JPS6010023B2 (ja) | 1985-03-14 |
| FR2322858B1 (enrdf_load_html_response) | 1981-04-30 |
| JPS5233621A (en) | 1977-03-14 |
| BE845867A (fr) | 1976-12-31 |
| IT1065479B (it) | 1985-02-25 |
| IE43417L (en) | 1977-03-08 |
| DE2639874C2 (de) | 1985-06-05 |
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